반응 #313498

반응 방정식

1-chloro-3-(triphenylphosphoranylidene)acetone

ethyl glyoxylate

→

ethyl (2E)-5-chloro-4-oxo-2-pentenoate

수율 47.8%

용매

dioxane

반응 조건

후처리

1. 1
   기타The solvent was removed by concentration
2. 2
   기타The residue was purified by column chromatography on silica gel using
3. 3
   workup.ADDITIONa mixture of chloroform and hexane (1:1 v/v) as an eluent
4. 4
   workup.ADDITIONThe eluted fractions containing the desired product
5. 5
   기타were collected
6. 6
   기타evaporated in vacuo

실험 절차

The mixture of 1-chloro-3-(triphenylphosphoranylidene)acetone (6.6 g) and ethyl glyoxylate (50% in toluene, 4.6 g) in dioxane (66 mL) was stirred at 80° C. for 1.5 hour. The solvent was removed by concentration. The residue was purified by column chromatography on silica gel using a mixture of chloroform and hexane (1:1 v/v) as an eluent. The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl (2E)-5-chloro-4-oxo-2-pentenoate (1.58 g).

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